Phenol, 4-amino-, 1-acetate → 1-Acetyl-2-methyl-4-[(4-acetoxyphenyl)imino]-1,2,3,4-tetrahydroquinoline

HRID 1629668

Reaktionsgleichung

Reaktionsgleichung von HRID 1629668
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2].[C:16]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[N:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:16](=[O:18])[CH3:17])=[CH:26][CH:25]=2)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 83783Phenol, 4-amino-, 1-acetateHCID 5895634(1H)-Quinolinone, 1-acetyl-2,3-dihydro-2-methyl-

Produkt 1

HCID 666259871-Acetyl-2-methyl-4-[(4-acetoxyphenyl)imino]-1,2,3,4-tetrahydroquinolineAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

[Step 1] 100 mg of 1-acetyl-4-oxo-2-methyl-1,2,3,4-tetrahydroquinoline and 227 mg of 4-acetoxyaniline were dissolved in 3 mL of toluene, and 250 μL of titanium tetrachloride (1.0 M dichloromethane solution) was added to the solution under ice cooling. The mixture was stirred for one hour under ice cooling, and then was stirred for another one hour at room temperature. After completion of the reaction, the reaction liquid was filtered through Celite and was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (chloroform), and thus 50 mg (30%) of 1-acetyl-2-methyl-4-[(4-acetoxyphenyl)imino]-1,2,3,4-tetrahydroquinoline was obtained as a yellow soup-like substance.

Aufarbeitung

  1. stirringwas stirred for another one hour at room temperature
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. filtrationwas filtered through Celite
  5. concentrationwas concentrated under reduced pressure
  6. customThe resulting residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-e74c9e2b9678404b9d9f4d82316f3a1b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791090B2

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